A cantilevered umbrella assembly with arcuate guide track comprises a support column, a cantilever arm attached to the support column, and an at least partially acrcuate configured guide track attached to the cantilever arm that defines a sweep axis and a plane. The guide track defines a first free end, a second free end and an apex between the first end and the second end along the sweep axis. The sweep axis defines a first tangent to the sweep axis at the first end, a second tangent at the second end, and a third tangent at the apex, wherein a first line drawn perpendicularly to the third tangent form a first included angle in the plane of the guide track that ranges from 10 to 45 degrees.